Sodium Bicarbonate → tert-Butyl (3R)-4-Hydroxy-3-phenylmethylbutanoate

HRID 373658Notes

Reaction equation

HRID 373658 reaction equation
[C:1]([O:5][C:6]([CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>O1CCCC1>[OH:11][CH2:10][C@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 13584974(2R)-2-Benzyl-4-tert-butoxy-4-oxobutanoic acid

Product 1

HCID 54261571tert-Butyl (3R)-4-Hydroxy-3-phenylmethylbutanoateYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the resultant acid from Example 99 (1.03 g, 3.90 mmol) in tetrahydrofuran (4 ml, THF) at 0° C. was added BH3 in THF (5.8 ml, 5.8 mmol, 1.0 molar) over 2 min. After 2 h at 0° C. the mixture was brought to room temperature and stirred for 2 h. The reaction was poured into saturated NaHCO3 solution and extracted into ethyl acetate which was dried over Na2SO4 and evaporated. Chromatography of the residue on silica gel with ethyl acetate/hexane mixtures afforded 0.55 g (56%) of the desired product as an oil. 1H NMR (CDCl3, TMS) δ 7.15-7.35 (m,5H), 3.65 (m,1H), 3.52 (m,1H), 2.65 (m,2H), 2.30 (m,2H), 1.90 (m,1H), 1.46 (s,9H).

Workup

  1. extractionextracted into ethyl acetate which
  2. dry with materialwas dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-a1c99c477fe04dea991289fc55f8d294
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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